Bromine → HCID 10495279, compound

HRID 234253Notes

Reaction equation

HRID 234253 reaction equation
[CH:1]([NH:3][C:4]1[C:9]([CH3:10])=[C:8]([CH2:11][C:12]([CH3:14])=[CH2:13])[C:7]([OH:15])=[C:6]([CH3:16])[C:5]=1[CH3:17])=[O:2].C([O-])(=O)C.[Na+].[Br:23]Br>C(O)(=O)C>[Br:23][CH2:13][C:12]1([CH3:14])[CH2:11][C:8]2[C:9]([CH3:10])=[C:4]([NH:3][CH:1]=[O:2])[C:5]([CH3:17])=[C:6]([CH3:16])[C:7]=2[O:15]1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 10537603HCID 10537603, compound

Product 1

HCID 10495279HCID 10495279, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Formylamino-2,3,5-trimethyl-6-(2-methyl-2-propenyl)phenol (50 g, 0.21 mol) and sodium acetate (30.5 g, 0.37 mol) were added to acetic acid (500 ml). Bromine (16.5 ml, 0.21 mol) was added dropwise to the mixture with stirring. After the reaction mixture was stirred for 30 minutes, the mixture was poured into ice water and the product was extracted with ethyl acetate. The extract was washed with aqueous saturated sodium bicarbonate solution, dried and then concentrated. The residue was dissolved in ethyl acetate again and insoluble materials were filtered off. The filtrate was concentrated and isopropyl ether was added to the residue. The crystals precipitated were filtered off to obtain the desired compound (44.0 g, yield: 65.7%), m.p. 157°-158° C.

Workup

  1. stirringAfter the reaction mixture was stirred for 30 minutes
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extract was washed with aqueous saturated sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate again
  7. filtrationinsoluble materials were filtered off
  8. concentrationThe filtrate was concentrated
  9. additionisopropyl ether was added to the residue
  10. customThe crystals precipitated
  11. filtrationwere filtered off

Sources & evidence

ORD record
ord-cbf7a3e48ae44c90a55556babd9f3141
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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